Bennington Vacations

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Find the Best Bennington Vacation Packages

Bennington Hotel Deals

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is ￥17,476 per night from Sep 2 to Sep 3
￥17,476
￥19,048 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Love this place"

Reviewed on Aug 15, 2025

Hotel Vervana, Trademark Collection by Wyndham
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is ￥17,033 per night from Aug 25 to Aug 26
￥17,033
￥18,566 total
Aug 25 - Aug 26
includes taxes & fees
7.6/10 Good! (882 reviews)
"The bed was the most comfortable ever. The pool was crystal clear and the breakfast was good. The clientele were very friendly and accommodating. Nice place!"

Reviewed on Aug 17, 2025

Best Western Bennington
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
The price is ￥13,100 per night from Aug 24 to Aug 25
￥13,100
￥14,279 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (598 reviews)
"I’ve said it before just wonderful people and place."

Reviewed on Aug 16, 2025

The Autumn Inn
See all 740 properties in Bennington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Bennington

Bennington Battle Monument showing landscape views

Bennington Battle Monument

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument

Bennington Potters Yard

You can do some window-shopping at Bennington Potters Yard during your stay in Bennington. Discover the coffeehouses and its art scene while you're in the area.

Bennington Potters Yard

Frequently asked questions

How much does a Bennington vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Bennington costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bennington?
You can generally find lower prices and greater availability in January, March and November. Browse our cheap Bennington vacation packages and you could land some great off-season discounts.
How many days is enough for Bennington?
With about 2 days, you'll have plenty of time to experience popular neighborhoods like Old Bennington and South Shaftsbury during your Bennington vacation. Remember to also add Norman Rockwell Exhibition and Robert Frost Stone House Museum to your list of must-sees. Looking for more adventures? Consider venturing outside of Bennington on day trips and tours.
Is it worth booking a vacation package to Bennington?
Bennington is a good vacation destination with attractions like Bennington Battle Monument among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Bennington vacation promises a good time for everyone.
How to find the best Bennington package deals?
Finding a cheap Bennington package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bennington vacation as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Bennington?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Bennington adventure.
How to plan a trip to Bennington?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Bennington.
  2. Plan your budget wisely: As well as the price of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may arise during your trip to Bennington.
  3. Decide how long to go for: Now that you're more familiar with Bennington, you can figure out the right length of your break. Create a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Bennington vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.